Process of making the monoformyl derivative of 1-3 dimethyl 4-5 diamido 2-6 dioxypyrimidin.



UNITED STATES Patented October 6, 1903.

PATENT OFFICE.

MAX ENGELMANN, OF ELBERFELD, GERMANY, ASSIGNO R TO FARBEN- FABRIKEN OF ELBERFELD CO., OF NEW YORK, N. Y., A CORPORA- TION OF NEW YORK.

PROCESS OF MAKING THE-MONOFORMYL DERIVATIVE F 1-3 DIMETHYL 4-5 DIAMIDO 2-6 DIOXYPYRlMlDlN.

SPECIFICATION forming part of Letters Patent No. 740,636, dated October 6, 1903.

v Application filed July 10,1903. Serial No. 165.001. (Lilo specimens.)

To all whom it may concern:

Be it known that I, MAX ENGELMANN, doctor of philosophy, chemist, residing at Elberfeld, Germany, (assignor to the FARBENFA- BRIKEN OF ELBERFELD 00., of New York,) have invented a new and useful Improvement in Processes of Making the Monoformyl Derivative of 1-3-Diinethyll--Diamido-2-6- Dioxypyrimidin; and I do hereby declare the following to be an exact and clear description of my invention.

I have f ound that the monoformyl derivatives of 4-5-diamido-2-6-dioxypyrimidin and of 3-methyl-4-5 diamido-2-6-dioxypyrimidin having the formulzs:

lrTH-(EO NH-co :0 fi-NH-C-OH and do ferns-own muc nn, on,-1 r c-NH,

which are described in Berichzfe der Deutschen Chcmz'schen Gesellschaft, Vol. 33, pages 3044 and 3049, can be transformed into the monoformyl derivative of l-3-dimethyl-4-5-diamido-2-G-dioxypyrimidin of the formula:

1 CH3N-CO(6) 2500(5 -NH-C-0H CH3 (if) by the action of methylating agents, such as methyl iodid and alkali or the like. The reaction takes place at the ordinary temperature. Ari-excess of alkali is to be avoided, because the resulting pyrimidin derivative can be converted into theophyllin by' the further action of an alkali, as is shown in the United States Letters Patent No. 716,994, dated December 30, 1902.

The following examples will serve to illustrate the manner in which my invention can be carried into practical elfect.

Example '1: A solution prepared from eighty-five grams of monoformyl-diamidodioxypyrimidin, ten hundred and fifty cubic centimeters of normal caustic-soda lye, and three hundred cubic centimeters of water is brought into reaction with one hundred and sixty grams of methyl iodid at about from to 40 centigrade while continuously stirring. During the reaction the dimethyl derivative partly separates from the liquid. When the reaction is completed, the liquid is acidulated with acetic acid, and the resultingmixture is evaporated to dryness. From the rawmaterial thus obtained the monoformyl derivative of l-3 dimethyll-5-diamido-2-6-dioxypyrimidin is obtained in a pure state by a recrystallization from boiling water.

Example 2: In an autoclave a solution of ninety-two grains of the monoformyl derivative of 3-methyl-2-6-dioxy-4-5-diamidopyrimidin in five hundred and forty cubic centimeters of normal caustic-soda lye is gently heated with twenty-six grams of methyl chlorid while stirring. After about twenty-four hours the reaction is finished. The dimethyl derivative thus obtained is filtered off and purified bya recrystallization from boiling water.

The process proceeds in an analogous mannor if instead of methyl iodid or methyl chlorid other methylating agents are used.

Having now' described my invention and in What manner the same is to be performed, what I claim as new, and desire to secure by Letters Patent, is-

1. The process for the production of the monoformyl derivative of 1:3-dimetl1yl-ei-5- diamido-2-6-dioxypyrimidin, which process consists in first treating the monoformyl derivative of 4-5-diamido-2G-dioxypyrimidin consists in firsttreating 3-1nethy1-4-5-diamid0- In testimony whereof I have signed my 2-6-di0xypy1'imidin with methyl chlorid and name in the presence of two subscribing witeaustic-soda lye and then isolating the resultnesses.

ing inonoformyl derivative of 1:3-di1nethy1- MAX ENGELMANN. 5 4-5-diamido-2-6-dioxypyrimidin from the re- Witnesses:

action mass, substantially as hereinbefore de- OTTO KGNIG,

scribed. J. A. RITTERSHAUS. 

